433285-19-9

Upstream product

• 192655-69-9 dimethyl (S)-2-(benzylamino)pentanedioate 
• 100-52-7 benzaldehyde 
• 23150-65-4 L-glutamic dimethyl ester hydrochloride 
• 56-86-0 L-glutamic acid 
• 269717-62-6 dimethyl (-)-(S)-2-[N-benzyl-N-(2-chloroacetyl)amino]pentanedioate 

Downstream Products

• 433285-25-7 (S)-3-(1-benzylpiperazin-2-yl)propan-1-ol 
• 433285-18-8 methyl (S)-3-(1-benzyl-3,6-dioxopiperazin-2-yl)propionate 

Relevant academic research and scientific papers

Synthesis of chiral non-racemic 3-(dioxopiperazin-2-yl)propionic acid derivatives

Starting with the proteinogenic amino acid (S)-glutamate (3) a facile, high yielding synthesis of the chiral non-racemic 3-(dioxopiperazin-2-yl)propionates 6, 11, and 14 is presented. Key intermediates in the synthesis of N1-benzyl substituted (dioxopiperazin-2yl)propionates 11 and 14 are the N-monobenzylglutamate 8 and the chloroacetamide 12, which allow introduction of various substituents in position 4 of the piperazine ting. In receptor binding studies with radioligands the 3-(piperazin-2-yl)propanol 15 was found to have promising affinity for σ1-receptors (Ki=66.1 nM).